Triethylamine → 1-Benzyloxycarbonylamino-3-methoxy-2-propanol

HRID 1729320Notes

Reaction equation

HRID 1729320 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH:10]([OH:14])[CH2:11][O:12][CH3:13].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.C(OCC)(=O)C>[CH2:15]([O:22][C:23]([NH:8][CH2:9][CH:10]([OH:14])[CH2:11][O:12][CH3:13])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 1245101-Amino-3-methoxypropan-2-ol

Product 1

HCID 190124911-Benzyloxycarbonylamino-3-methoxy-2-propanolYield 56.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

19.69 g of triethylamine are added to a solution of 10.23 g of 1-amino-3- methoxy-2-propanol in 100 ml of tetrahydrofuran. After the mixture is cooled, a solution of 16.60 g of benzyloxycarbonyl chloride in 50 ml of tetrahydrofuran is added dropwise thereto for 30 minutes. The mixture is stirred at room temperature for one hour. The reaction mixture is diluted with ethyl acetate, washed with water and dried. The residue is purified by silica gel column chromatography [solvent: ethyl acetate - hexane (2:1)]. 13.2 g of 1-benzyloxycarbonylamino-3- methoxy-2-propanol are obtained as colorless oil.

Workup

  1. temperatureAfter the mixture is cooled
  2. washwashed with water
  3. customdried
  4. customThe residue is purified by silica gel column chromatography [solvent: ethyl acetate - hexane (2:1)]

Sources & evidence

ORD record
ord-7a671331d9fe4131b211b8303ad558e2
Source dataset
uspto-grants-1994_07
Patent number
US05332754

Reaction notes

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